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Top Destinations in Virginia to Visit This Holiday Season 2021


Written by Emily Bayne

Veterinary reviewed by:

Published: 11/22/2021, edited: 11/22/2021


When November comes to an end, towns all over Virginia transform into a winter wonderland. Pet families come from near and far to experience Virginia's festive ambiance and dog-friendly holiday celebrations. But with so many pet-friendly attractions and events, it can be tough to decide where to visit. Luckily, we've done some digging to find the best stops in Virginia so you have the happiest of holidays!

German Shepherds feeling the holiday spirit at a home

Downtown, Charlottesville

The holiday spirit is contagious in the city of Charlottesville. Between the extravagant festivities and pet-friendly establishments, there's plenty of Christmas cheer to go around in this city! 

  • The holiday celebration begins with The Grand Illumination ceremony, which takes place at 5 pm on December 3rd. The ceremony is entertaining for all ages (and species!) with inflatables, food and craft vendors, and even train rides for the kiddos. After the streets are lit, the real fun begins! Good Shot Judy, a local swing band, will take the stage and entertain crowds with Christmas classics. Vendors will ensure crowds can eat, drink, and be merry into the night.  

  • Have some last-minute holiday shopping to do? Take your pup to peruse shops alongside you at Charlottesville Historic Downtown Mall. A lot of stores are super pet-friendly and even set out water dishes for their furry patrons. Check with each store before entering to make sure woofers are allowed in that particular establishment.

  • After a long day of shopping, head over to Azalea Dog Park for some leash-free playtime with your pooch. This is one of the most "pawpular" parks in the city, so you and your pack are bound to make some friends during your visit. 

  • If your holiday itinerary gets hectic, "un-wine" with a trip to one of Charlottesville's many dog-friendly wineries like Pippin Hill Farm and Vineyards. At Pippin Hill, pet parents with leashed fur-babies can sip to their hearts; content in the outdoor areas of the winery, though you'll have to leave Fido behind to participate in their guided wine tastings.

Old Town Alexandria, Alexandria

Alexandria, Virginia, outdoes itself every holiday season with elaborate parades and lavish holiday bashes. From the Scottish Walk Parade to the Waterskiing Santa Event, there is something to look forward to the whole month of December! 

  • For one of Virginia's most unique parade experiences, check out Alexandria's Scottish Walk Parade on December 4th at 11 am. Bagpipe music fills the air as tartan-clad Scottish clan members march down the streets to celebrate the city's founding by Scottish immigrants. The best part? Proceeds from the Scottish Walk festivities benefit the Campagna Center, a nonprofit that provides local families educational resources. 

  • Alexandria’s Holiday Boat Parade of Lights is an iconic celebration that is set for December 4th. The parade won’t begin until 5:30 pm, but the celebration starts at 2:00 pm with fun kids' activities, an assortment of food vendors, hot cocoa stations, and local beer. If you have children, pop over to the Penny Post tent so your little ones can scribble a note to Santa, or stop into the AR Workshop tent where they can bedazzle their very own tree ornament! When the parade begins, your pack will watch in amazement at all the lighted boats and cheer for joy when Santa Paws makes his appearance on the city’s fireboat. 

  • Speaking of Santa, did you know Alexandria is home to a Waterskiing Santa Event? Yes, you read that correctly. Stop by the Waterfront Park on Christmas Eve at 1:00 pm for a glimpse at Santa and his helpers skimming across the Potomac on skis! 

  • If all those holiday celebrations have your dog craving an off-leash romp, check out Monticello Park Off-Leash Dog Area on Beverly Drive. Keep in mind this dog park isn’t fenced, so you may want to keep Sparky on leash if they have poor recall skills.

Greater Williamsburg, Williamsburg

Travel + Leisure Magazine ranked Williamsburg one of the top 20 "Best Towns for the Holidays" in America, and rightfully so! This city has it all — historic sites, parades, shopping, great restaurants — and the best part is most of these establishments and events are dog-friendly!

  • The 57th annual Williamsburg Christmas Parade is sure to spread Christmas cheer to your pack. The live entertainment is always a hit, and parade participants go all out embellishing their floats with festive decor and lights. While watching, keep an eye out for Santa Paws!

  • Enjoy a blast from the past with a family trip to Colonial Williamsburg. Here, you'll get the chance to see how colonial life was, watch artisans work, explore archeological sites, and see replicas of historic buildings. Pups are welcome to explore the outdoor sights and smells of Colonial Williamsburg, just not inside the historic buildings. Colonial Williamsburg is even more magical during the holiday season with all the beautiful decorations.

  • The highlight of the holidays in Colonial Williamsburg is the Grand Illumination ceremony. The ceremony will be held for the first 3 weekends in December. Packs can enjoy live 18th-century musical performances, plays, and even a firework show! Keep in mind this is a large pyrotechnic display that may frighten some dogs. Use your best judgment when bringing Fido along for this adventure. Check out this article for information on training dogs to accept fireworks

  • See if you can spot the ghosts of Christmas past with a dog-friendly tour by Colonial Ghosts. With Colonial Ghosts tours, you'll get a history lesson and paranormal stories, making it a holiday experience like no other!

  • Need a little retail therapy after all that excitement? Stop by local dog-friendly shops like Barnes and Noble and the Williamsburg General Store for some holiday shopping with your fur-baby.

Atlantic Avenue, Virginia Beach

The beach may not be the first destination that comes to mind when you think of holiday travel, but we promise Virginia Beach won't disappoint. This city is part of 100 miles of lights that extends to Richmond and boasts some of the most impressive displays in the state. 

  • With live entertainment, massive helium balloons, costumed characters, and dozens of themed floats, the Holiday Parade at the Beach will definitely impress your pack! The fun begins at 5:30 pm on December 4th. 

  • A holiday trip to Virginia Beach isn't complete without a drive down the Holiday Lights Merry Mile. This unique light display is synchronized with holiday music and features glowing sea life as well as more traditional Christmas decor. Streets become aglow from November 25th to December 31st from 5:30 pm to 10 pm most days and until 11 pm on Saturdays. 

  • If seeing all the hot cocoa and holiday treats have your dog craving a sweet treat of their own, head over to Salty Paws Ice Cream and Bakery. This adorable pup bakery serves up doggy dishes like ice cream and biscuits that your dog can safely enjoy. 

  • First Landing State Park Beach is a "furrific" place to spend the day with your crew. In fact, we feel so strongly about this that we included it on our list of top dog parks in Virginia Beach. As its name suggests, this historic beach is where English settlers first landed in Virginia. This park checks all the boxes for a family fun day with a beautiful dog-friendly beach, 20 miles of scenic nature trails, and educational opportunities.

Downtown, Richmond

The holidays are a big deal in Virginia's city capital of Richmond. With two parades, tree decorating competitions, and dazzling illumination ceremonies, this city will make your Christmas merry and bright!

  • Watch the city of Richmond burst into color at the RVA Illuminates event on December 3rd at 5:45 pm. The festivities will take place at Kanawha Plaza on East Canal Street, but ABC8 News will air it live for those who can't attend.  

  • The Annual Dominion Energy Christmas Parade goes all out with music, dancing, dazzling floats, children's characters, and the one and only Santa Claws. The party starts at 10:00 am on December 4th and will begin at the Science Museum of Virginia. 

  • Support local nonprofit organizations and view meticulously decorated holiday trees at ​​Christmas Under the Clocktower at Main Street Station. The main event will happen on December 3rd at 7:00 pm, but online voting for the best tree extends until December 19th. The event is free to attend, so show up and show your support for local charities! 

  • After being canceled due to COVID concerns in 2020, Richmond Boat Parade of Lights will be returning for the 2021 holiday season. The festive boats will set sail on December 11th at 5:30 pm. Cozy up with some warm cider and your fur-baby at Rocketts Landing for the best viewpoint.

  • Reward Fido for their good behavior with some off-leash activities at Ruff House Dog Park in Rockwood Park. The park boasts separate play areas for active and timid dogs to ensure pets are surrounded by dogs with similar playstyles. This adorable park will definitely bring your pack some holiday cheer!

As pet parents, we would love to bring our pets along on all our adventures, though that isn't always an option. If you've got plans for an event that doesn't allow dogs, let Wag! help.

Wag! will connect you with professional dog sitters in your area who will dote on Fluffy in your absence. Whether you're local or staying in a hotel, sitters with Wag! will come to your pet and take care of them while you're out. Book a dog sitting appointment with Wag! today!

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